Potassium Carbonate → 3-[5-(2-Chloro-4-methoxyphenoxy)pentyl]-5-methylisoxazole

Participants

Reaction Steps

A mixture of 5.5 g (0.0345 mole) of 2-chloro-4-methoxyphenol, 8.0 g (0.0345 mole) of 3-(5-bromopentyl)-5-methylisoxazole (Example 40i), 6 g of potassium carbonate, 0.1 g of potassium iodide and 75 ml of acetonitrile was heated at reflux for 24 hours. The reaction mixture was filtered, concentrated in vacuo, dissolved in 50 ml of methylene dichloride, filtered and again concentrated. The residue was distilled at 135°-200° C.(0.2 mm) and then redistilled, collecting the fraction boiling at 170°-190° C.(0.05 mm). The product crystallized and was recrystallized from ether--pentane to give 5.2 g of 3-[5-(2-chloro-4-methoxyphenoxy)pentyl]-5-methylisoxazole, m.p. 45°-47° C.; MIC vs. rhinovirus Type 2=0.7 μg/ml; and vs. polio-2 virus=1.4 μg/ml.

Provenance & Evidence